(2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

Base Information

Chemical Name:(2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol
CAS No.:99096-90-9
Molecular Formula:C₁₉H₃₂O₃Si
Molecular Weight:336.547
Hs Code.:

Synonyms:(2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

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Chemical Property of (2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

Chemical Property:

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Technology Process of (2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

There total 1 articles about (2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 98944-53-7
(S)-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-D-glyceraldehyde

: 762-72-1
allyl-trimethyl-silane

: 99096-89-6
(2R,3R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

: 99096-90-9
(2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 - -10 ℃; Yield given. Yields of byproduct given;
DOI:10.1021/jo00225a103

Reference yield: 81.0%

: 100-39-0
benzyl bromide

: 99096-90-9
(2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

: (((2R,3S)-2,3-bis(benzyloxy)hex-5-en-1-yl)oxy)(tert-butyl)dimethylsilane

Guidance literature:: (2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 8h; Inert atmosphere;
DOI:10.1515/hc-2019-0015

Reference yield:

: 99096-90-9
(2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

: 66018-41-5,69427-14-1
zeaenol

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 8 h / 0 - 20 °C / Inert atmosphere

2.1: camphor-10-sulfonic acid / methanol / 12 h / 0 - 20 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: diethylzinc / toluene / 1 h / Reflux; Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

4.3: 12 h / 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

7.1: potassium carbonate; palladium diacetate; tetrabutylammomium bromide; triphenylphosphine / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere

8.1: camphor-10-sulfonic acid / methanol / 1 h / 20 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

10.1: chloro-trimethyl-silane; methanol / 20 °C / Inert atmosphere

11.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

12.1: methanol / 10 h / Inert atmosphere; Alkaline conditions

13.1: titanium tetrachloride / dichloromethane / 0 °C / Inert atmosphere

With methanol; lithium aluminium tetrahydride; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; tetrabutylammomium bromide; diethylzinc; palladium diacetate; titanium tetrachloride; sodium hydride; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 7.1: |Heck Reaction / 11.1: |Mitsunobu Displacement;
DOI:10.1515/hc-2019-0015